Hydrochloric Acid → 4-(3-Fluoro-4-methoxyphenyl)-1,2,3,6-tetrahydropyridine hydrochloride

Participants

Reaction Steps

A solution of tert-butyl 4-(3-fluoro-4-methoxyphenyl)-4-hydroxypiperidine-1-carboxylate (0.5 g, 1.5 mmol) in 1,4-dioxane (20 mL) was chilled to 0° C. and treated with a solution of HCl in 1,4 dioxane (4.0 M, 10 mL, 40 mmol). The reaction mixture was stirred at rt for 12 h, and then the solvents were removed to provide a crude compound which was triturated with diethyl ether to provide the desired product as a solid (1.2 g, 82%). LC/MS (Method 109) RT=1.798 min. (M+H)+=207.8; 1H NMR (300 MHz, DMSO-d6) δ 9.51-9.09 (m, 2H), 7.00 (d, J=8.3 Hz, 1H), 6.79-6.71 (m, 2H), 5.52 (t, J=1.5 Hz, 1H), 3.73 (s, 3H), 3.67 (br. s., 2H), 3.26 (d, J=4.5 Hz, 2H), 2.45 (d, J=1.9 Hz, 2H), 2.25 (s, 3H)

Provenance & Evidence